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Stapleton was mentioned in the Domesday Book of 1086.[1] Though it has been known that a settlement has existed on this sharp bend in the river since the 9th century. The name originates from the Old English words 'stapol' meaning boundary post and 'tun' meaning settlement, and is pronounced locally as 'Stapp-l-ton'.[2] The village and surrounding area were granted by William the Conqueror to a knight who would become known as Benedict de Stapleton, by the 13th century the now powerful 'de Stapleton' family gave some lands around the village to the nearby Premonstratensian monks of Easby Abbey and in so doing forgoing the obligation to maintain a ferryboat across the river. One member of the Stapleton family, Miles Stapleton of Bedale was one of the founding members of the Order of the Garter. The family built a manor in the village as well as a private chapel named after St. James, the settlement had second church known as St. Leonard's administered by Easby Abbey. Neither the Manor or the two churches exist today, local speculation suggests that the site of the manor is located in 'Garth Field', the irregularity of the land being the last remnants of a defensive moat or pond. By 1616 the Stapleton family had left the village and the churches fell out of use, this is thought to be the origin of the 'Corpse Walk' as when the church at Croft was used for burials, the deceased had to be carried between the two villages a distance of some three miles.[3]

During the medieval period a bridge existed linking the village to the northern bank of the river and presumably replaced the ferryboat, it is believed that from this the Public House in Stapleton, 'The Bridge Inn' is named. This bridge however was lost after a flood and was not replaced, meaning that the nearest crossing was at Croft-on-Tees until 1833 when the Blackwell bridge was built.

More recent history has seen the picturesque village as the filming location of the war film Way to the Stars. Until the second half of the 20th century the village was served by a Post Office, a blacksmith and a public house. Only the latter is still in use.

Stapleton rests within an area made renowned by the Marquess of Zetland's Hunt characterised by rolling countryside and river rock masonry synonymous with the Richmondshire district. From the top of Stapleton bank panoramic views can be seen, ranging from the Cleveland and Hambledon Hills in the east to the Yorkshire Dales and Teesdale in the west. The village lies around 10 miles north of Richmond, 15 miles from the county town Northallerton and 4 miles south of the market town Darlington. Like many villages in this area of North Yorkshire and of its age Stapleton is centred on a large village green, similar to that of nearby Aldbrough St John and Barton.